In 2013, a 21-year-old emailed Mark Cuban from a Motel 6 after watching Shark Tank.
Cuban replied in 45 minutes.
That cold email eventually led to 230M+ in funding an AI company that predicts laws before Congress.
How a 5-line cold email started it all 🧵
That 21-year-old was Tim Hwang. At 17, he was elected to Maryland's Board of Education, overseeing a billion budget.
At 19, he founded the National Youth Association with 750,000 members.
But his work on Obama's campaign exposed a government problem nobody had solved...
(Tim with NVIDIA's Jenson Huang 👇🏻)
The problem? Government data was scattered across thousands of disconnected systems.
No one could effectively track policy changes affecting citizens, businesses, or advocacy groups.
A simple question became Tim's obsession and led to the founding of FiscalNote.
FiscalNote's early days were brutal:
Three founders in a /night Motel 6 room working 24/7.
Two beds between them (even slept on floors).
Attending tech meetups just for free food.
They almost gave up countless times.
What changed everything?
One Friday night, exhausted from coding, Tim and team took a break to watch Shark Tank.
As the episode ended, Tim had a wild thought.
"We should just email Mark Cuban."
No connections. No intro. No track record.
Just a simple 5-line email.
Tim's email was ruthlessly simple:
- Problem: Government data is broken
- Solution: Our AI predicts policy outcomes
- Early proof: Working prototype
- Ask: Investment consideration
- Unique advantage: Strong team
No marketing language. No fluff.
Cuban responded in 45 minutes.
Tim's team dropped dinner, rushed to their laptops, and answered Cuban's questions.
Within weeks, he wrote a 0,000 check.
That first "yes" triggered a series of investments from Jerry Yang, NEA, and First Round.
All from a cold email that took 5 minutes to write.
Today, FiscalNote ($NOTE) is a publicly-traded company:
- Their AI analyzes laws across 2,800+ cities & 500 federal bodies
- 4,000+ organizations rely on their tech
- Acquired CQ Roll Call for 0M
- 500+ employees in global offices
All from one cold email.
But what made Cuban respond when thousands of pitches fail?
Tim's pitch had perfect relevance to Cuban's investment interests:
A data problem that tech could solve
Evidence of early traction
A solution disrupting an outdated industry
Today? This email would never reach his inbox.
The brutal reality of cold email in 2025:
* 70% of cold emails are ignored or end up in spam
* 16% of emails never even reach the inbox
* Domain reputation trumps subject lines
* Basic personalization gets ignored
Yet some companies still dominate with outbound. Here's how:
At ColdIQ, we design outbound systems for how buyers behave in 2025:
- Build proper infrastructure FIRST (domain setup, warm-up protocols)
- Target based on specific triggers, not static lists
- Execute multi-channel sequences that reinforce each other
- Relevance > personalization
This system is how we scaled ColdIQ to .5M ARR in just 2 years.
We started with ,500/month clients.
Today we regularly close ,000+ MRR deals.
The fundamentals of cold outreach haven't really changed, but execution has transformed completely.
That's where the edge lies.
Remember: Cold email isn't dead – lazy outbound is.
Tim's email to Cuban worked because he spoke directly to a problem worth solving.
That fundamental hasn't changed. But the technical barriers to reaching decision-makers have multiplied exponentially.
Delivery is now just as strategic as the message itself.
Thanks for making it to the end!
A little about me:
I built a .5M ARR business proving cold email still works.
Started in a cramped Berlin flat during lockdown. Now running global teams across 10 countries, remotely.
Currently COO @ ColdIQ (
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